Search Villas in Chesapeake Bay

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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Villas in Chesapeake Bay

Quiet Villa with Bowling Alley, Pools, +Mini Golf
Interior

Quiet Villa with Bowling Alley, Pools, +Mini Golf

9.0 out of 10, Wonderful, (2)
"Loved this centrally located place. It was nestled between Jamestown and Williamsburg. The accommodations were very clean and provided everything we needed."
Quiet Villa with Bowling Alley, Pools, +Mini Golf
The Boat House on the Bay - On the water; Pet Friendly; WiFi
View from property

The Boat House on the Bay - On the water; Pet Friendly; WiFi

8.4 out of 10, Very Good, (18)
"Another fun vacation in the books."
The Boat House on the Bay - On the water; Pet Friendly; WiFi
Washington Family Property, Upper Carriage House in Old Town on 107 S Lee Street
Fridge, microwave, oven, stovetop

Washington Family Property, Upper Carriage House in Old Town on 107 S Lee Street

9.8 out of 10, Exceptional, (18)
"The house was great Perfect for two people and in a great location. "
Washington Family Property, Upper Carriage House in Old Town on 107 S Lee Street
Quiet Villa with Access to Amazing Amenities
Interior

Quiet Villa with Access to Amazing Amenities

8.8 out of 10, Excellent, (3)
"Excellent"
Quiet Villa with Access to Amazing Amenities
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

How much do villas in Chesapeake Bay cost?
Prices for villas in Chesapeake Bay range between and per night. Whatever your budget, you're sure to find a place that suits your needs on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Chesapeake Bay?
Choose from villas in Chesapeake Bay. Whether you're escaping with relatives or a group of pals, and wherever your travels take you, Expedia can help you secure your perfect fit.
Why book your villa in Chesapeake Bay with Expedia?
Reserving a villa in Chesapeake Bay is as simple as working out your travel dates and picking the option that satisfies your needs. Want something affordable or upmarket, or a stay that also comes with a laundry and kitchen? Use Expedia's search filters to narrow your results and find the perfect fit.